EP0839797B1 - Procédé pour la préparation du 2-méthyl-2,4-diaminopentane - Google Patents

Procédé pour la préparation du 2-méthyl-2,4-diaminopentane Download PDF

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Publication number
EP0839797B1
EP0839797B1 EP97118409A EP97118409A EP0839797B1 EP 0839797 B1 EP0839797 B1 EP 0839797B1 EP 97118409 A EP97118409 A EP 97118409A EP 97118409 A EP97118409 A EP 97118409A EP 0839797 B1 EP0839797 B1 EP 0839797B1
Authority
EP
European Patent Office
Prior art keywords
catalyst
diaminopentane
methyl
reactor
acetone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP97118409A
Other languages
German (de)
English (en)
Other versions
EP0839797A1 (fr
Inventor
Helmut Dr. Waldmann
Jürgen Dr. Dahmer
Anatoly Prof. Bazanov
Alexandre Dr. Timofeev
Natalja Dr. Zubritskaya
Gennady Prof. Terechtchenko
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0839797A1 publication Critical patent/EP0839797A1/fr
Application granted granted Critical
Publication of EP0839797B1 publication Critical patent/EP0839797B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds

Definitions

  • the invention relates to a process for the preparation of 2-methyl-2,4-diaminopentane from 2,2,4,4,6-pentamethyl-2,3,4,5-tetrahydropyrimidine, 2-methyl-2,4-diaminopentane is an important intermediate, e.g. for paint raw materials.
  • ion exchange resins as a catalyst for Manufacture of pyrimidines, i.a. Acetonin is also in US-A-3,904,625 known.
  • DE-B-1 276 041 describes a further catalyst system Extraction of acetone from acetone and ammonia is taught.
  • the invention relates to a process for the preparation of 2-methyl-2,4-diaminopentane, characterized in that acetone, ammonia and hydrogen at a temperature of 20 to 130 ° C and at pressures of 30 to 250 bar by a two-zone catalyst are passed, the first zone being filled with a NH 4 ⁇ group- containing cation exchange resin or a catalyst which consists of aluminum oxide and / or silicon oxide and then consists of a nickel-containing hydrogenation catalyst in the second zone.
  • acetone or compounds can be used which are provide acetone to the reaction conditions or are formed from acetone, e.g. Diacetone alcohol, acetone imines such as acetone imine, etc.
  • the reaction is carried out at a temperature of 20 to 150 ° C, preferably 50 to 130 ° C, carried out at a pressure of 10 to 300 bar, preferably 30 to 250 bar.
  • the method according to the invention is carried out in two zones.
  • a conventional sulfonated cation exchange resin in the NH 4 form or Al or Si oxides as the catalyst and in the second zone a catalyst which contains 30-60% by weight of nickel and / or copper on chromium oxide.
  • the starting materials acetone or substances which provide acetone under the reaction conditions, ammonia and hydrogen are brought into a first reaction zone which contains sulfonated polystyrene resin in the NH 4 form and then passed into a second zone which is used as Catalyst containing nickel on chromium oxide, which was loaded with hydrogen before the start of the reaction.
  • Two reactors with fixed bed catalysts, which are connected in series, are used to carry out the process.
  • the first reactor was charged with 200 cm 2 of a sulfonated polystyrene cation exchange resin in the NH 4 form (Ku-2-8) and the second reactor with 500 cm 2 of a reduced catalyst which contained 48% by weight of nickel on chromium oxide.
  • Acetone was fed from below into the first reactor at a flow rate of 50 ml / h and liquid ammonia at a flow rate of 20 ml / h, the temperature being kept at 20 to 30 ° C. (room temperature) and the pressure about 50 bar was.
  • the reaction mixture had passed the first reactor, the mixture was heated to 120 ° C. and passed into the second reactor together with liquid ammonia (150 ml / h) and hydrogen (200 l / h).
  • the temperature in the second reactor was 120 ° C. at a pressure of 200 bar.
  • Example 1 The procedure was carried out as in Example 1.
  • the first reactor was charged with 200 cm 2 of a catalyst containing 17% by weight of Al. Contained 2 O 3 on silica gel as a catalyst.
  • the second reactor was filled with 200 cm 2 of a catalyst which contained 46% by weight of nickel and 17% by weight of copper on chromium oxide.
  • the catalyst in the second reactor was reduced with hydrogen.
  • acetone and liquid ammonia were introduced at a rate of 10 ml / h from the bottom into the first reactor, at a temperature of 90 ° C and then into the second reactor at a temperature of 130 ° C, the pressure in both Reactors was 100 bar.
  • reaction mixture was passed through the first reactor, it was taken together with ammonia at a rate of 30 ml / h and hydrogen introduced into the second reactor at a rate of 100 l / h.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)

Claims (1)

  1. Procédé de préparation du 2-méthyl-2,4-diaminopentane, caractérisé en ce que l'on envoie de l'acétone, de l'ammoniac et de l'hydrogène à une température de 20 à 130°C sous des pressions de 30 à 250 bar sur un catalyseur à deux zones, la première zone étant garnie d'une résine échangeuse de cations à groupes NH4 ⊕ ou d'un catalyseur consistant en un mélange d'alumine et/ou de silice, la deuxième zone consistant ensuite en un catalyseur d'hydrogénation qui contient du nickel.
EP97118409A 1996-11-05 1997-10-23 Procédé pour la préparation du 2-méthyl-2,4-diaminopentane Expired - Lifetime EP0839797B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19645549A DE19645549A1 (de) 1996-11-05 1996-11-05 Verfahren zur Herstellung von 2-Methyl-2,4-diaminopentan
DE19645549 1996-11-05

Publications (2)

Publication Number Publication Date
EP0839797A1 EP0839797A1 (fr) 1998-05-06
EP0839797B1 true EP0839797B1 (fr) 2000-05-31

Family

ID=7810688

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97118409A Expired - Lifetime EP0839797B1 (fr) 1996-11-05 1997-10-23 Procédé pour la préparation du 2-méthyl-2,4-diaminopentane

Country Status (5)

Country Link
US (1) US5801285A (fr)
EP (1) EP0839797B1 (fr)
DE (2) DE19645549A1 (fr)
ES (1) ES2148891T3 (fr)
RU (1) RU2198161C2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8466082B2 (en) 2007-05-31 2013-06-18 Sued-Chemie Ip Gmbh & Co. Kg PD/AU shell catalyst containing HFO2, processes for the preparation and use thereof

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GT200600350A (es) * 2005-08-09 2007-03-28 Formulaciones líquidas
DE102007025444A1 (de) * 2007-05-31 2008-12-11 Süd-Chemie AG VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung
DE102007025442B4 (de) 2007-05-31 2023-03-02 Clariant International Ltd. Verwendung einer Vorrichtung zur Herstellung eines Schalenkatalysators und Schalenkatalysator
DE102007025315A1 (de) * 2007-05-31 2008-12-11 Süd-Chemie AG Katalysator zur selektiven Hydrierung acetylenischer Kohlenwasserstoffe und Verfahren zu seiner Herstellung
DE102007025362A1 (de) 2007-05-31 2008-12-11 Süd-Chemie AG Dotierter Pd/Au-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung
DE102007025223A1 (de) 2007-05-31 2008-12-04 Süd-Chemie AG Zirkoniumoxid-dotierter VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung
DE102008059341A1 (de) 2008-11-30 2010-06-10 Süd-Chemie AG Katalysatorträger, Verfahren zu seiner Herstellung sowie Verwendung

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2486648A (en) * 1947-03-24 1949-11-01 Shell Dev Production of diamines
DE1276041B (de) * 1965-03-27 1968-08-29 Scholven Chemie Ag Verfahren zur Herstellung von 2, 2, 4, 4, 6-Penta-methyl-2, 3, 4, 5-tetrahydropyrimidin
US3904625A (en) * 1974-04-08 1975-09-09 Petrolite Corp Use of ion exchange resins in preparing tetrahydropyrimidines
US4652625A (en) * 1986-02-18 1987-03-24 Texaco Inc. N-aminopropyl derivatives of 2,4-diamino-2-methylpentane as epoxy curing agents

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8466082B2 (en) 2007-05-31 2013-06-18 Sued-Chemie Ip Gmbh & Co. Kg PD/AU shell catalyst containing HFO2, processes for the preparation and use thereof

Also Published As

Publication number Publication date
ES2148891T3 (es) 2000-10-16
RU2198161C2 (ru) 2003-02-10
US5801285A (en) 1998-09-01
DE59701804D1 (de) 2000-07-06
EP0839797A1 (fr) 1998-05-06
DE19645549A1 (de) 1998-05-07

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